Three weeks ago, I sailed away from New York City. I cast off the lines from our 37-foot sloop and left New York harbor for the East River, along with my husband and dog. In that moment, and without much ceremony, we were no longer New Yorkers. The moment we left the dock, we became full-time sailors with no homeport to call us back.
This wasn’t a longtime dream. We’re not lifelong boaters. Nor did we come from wealth or retire early on some startup exit. My husband, Jon, and I are simply wanderers. We spent years wanting something else. This is our else.
Before moving to New York two years ago, Jon and I met through our love of travel. After a couple of years of dating, we each began working without an office, for a total of about five years, sometimes running a business together, sometimes working separately. This wasn’t gig economy work but rather leadership positions for traditional companies that were trying a new format of working. And it worked. I completely and emotionally bought into the idea and lifestyle. It felt natural to me to pace my days around the work I needed to do and the life I wanted to live rather than a more traditional schedule.
While working this way, Jon and I lived by the flexibility to travel while getting things done. We rarely ever took vacations but instead set up in coffee shops while we were on the move, sometimes so flawlessly that the only way our coworkers would know was by the change in background when we video chatted.
But without jobs that tied us to a place, we kept having the same conversation: Where did we want to live, and what kind of people were we? Were we LA people? San Francisco people? Would we fit in better on the East Coast or somewhere in South America?
As all our friends started to settle down, finding the answer seemed more urgent — and that’s when we bought a boat. We had a home that could take us anywhere. We didn’t know anything about sailing. We bought the Scallywag without knowing how to use it or fix it and set our hearts on figuring it out together.
What we didn’t expect is that our boat would introduce us to a community. Sailors are people of different ages and means, united by a similar sense of adventure. It’s a way of life that makes you generous. With your time, because accepting a slower pace means you are forced to have lots of it. With your advice, because it feels imperative for other people to capture the magic of each thing you learn. And with your stuff, be it a meal for strangers or a box full of boat gear that feels too precious to toss. We found, with delight, that the sharing of wild yarns and the pace of storytelling is identical in both the worlds of travelers and sailors. This was a parallel world to the one that bound us when we met, but we didn’t have to go to far-flung reaches of the world to sail — it could be done almost anywhere.
Fast forward three years, and we found ourselves living in New York, pursuing huge steps in our careers in an amazing city where we could be anything and where our ambitions could run free but only in one place.
While our desire for success was satisfied more quickly than ever, we found New York a wonderful but tough place to live. The city provides limitless moments of wonder to all who visit and live there, but it offers a sense of place to very few. That’s to be expected — no place can hold so many big dreams on its shoulders without becoming hardened with the burden after awhile. We found the city made itself available to us, but it didn’t welcome us. For many, its indifference is a bright challenge. But to us, it was a tiring one.
As we hit the two-year mark of residency, we were once again itching for change. We thought the answer was to start taking interviews for jobs we could have only imagined being recruited for before we had arrived. But each time, we came home to each other and asked ourselves… then what? We have that awesome job and… then what?
The paradox of choice is a weird, wonderful and very “now” problem to have.On our first day at anchor, I drank a coffee and checked my email in a quiet bay in Long Island. As I write this, we’re anchored in the city of Newport.
As a woman who wants to have kids someday, I found this indecision particularly challenging. Smarter women than I have told me the key to a great work-life balance is to lock down a baller job a couple of years before having kids so that you have deeper job security for your maternity leave. But a really big part of my heart wanted to build a flexible career that kids could be warmly welcomed into rather than interrupt. I wanted to start that career before it was nine-months-urgent and continue it after, on my own time. And I wanted a lifestyle that could be shaped around what drove me instead of my drive to and from home.
So the answer for us, after a hundred conversations between Jon and myself about what we love to do and what we want our lives to look like now and as we grow older, is to pursue careers that don’t have geographic limits.
It’s never been a better time to go that route — most places finally have the infrastructure to support digital nomadism, and the speed with which things are changing is breathtaking. Five years ago, I got my first smartphone — while working in Iraq. During a recent fringe diplomacy trip to Myanmar, Jon and I learned that though the internet essentially didn’t exist there a year ago, there are now more people connected via smartphones than there are houses wired to an electrical grid.
And on a recent vacation to the French Caribbean, we found pockets of internet where fellow boaters said nothing had existed just months ago.
The ability to work anywhere and work well is here — even if it takes extra time and inconvenience to figure it out.
This is the freedom that today’s technology provides, and yet to embrace it can still make you an implausible hire and a weirdo.
So, we’re ready to be weirdos.
We’ve launched businesses (his, mine) that allow us to do the work we love while we travel, with the assumption that there will be frequent trips to metro hubs to see our clients face-to-face. We’ve outfitted our boat with solar panels, a wind generator, cell and WiFi boosters andwe’ve upped our data across multiple networks. And we’ve hungrily read the stories of people who have gone before us to figure out just how much we can pull off without risking our sanity and quality of work.
Our plan is to sail back to California — the long way. First north, perhaps as far as Nova Scotia, then south to the Caribbean and through the Panama Canal. We don’t have a set itinerary or time span, though we think it’ll take about a year. We’re excited to explore parts of this continent and its surrounding isles we’ve never seen before, to take it slow and to make lots of mistakes as full-time cruisers.
(Our first, for example, was to set a hard date for leaving, which we promptly blew after having a camera crew see us off. ::Facepalm::)
That’s our plan: subject to lots and lots of changes.
On our first day at anchor, I drank a coffee and checked my email in a quiet bay in Long Island. As I write this, we’re anchored in the city of Newport. I’ve been wearing t-shirts and shorts all week, we’ve been living ostensibly rent-free on our anchor and I’ve been taking conference calls from the deck of the boat.
Then again, I’m covered with bruises and blisters that come with living into cruising life – from clambering around the boat, hauling rope and generally existing on a thing that is constantly moving and begets “boat bites.” Today, a simple grocery trip involved hauling a cart full of grocery bags from store to borrowed car to dinghy for a windy wet ride across the bay.
Cruising won’t be easy. Neither will running a business remotely. But it’s possible, and that’s enough for me to wend my way into the unknown with full sails and no regrets.